Reaction conditions: HAA reactions of 2-alkylfurans with aldehyde to FL were conducted using 0.05 g of Aquivion PW98, 10 mmol 2-alkylfuran, and 5 mmol aldehyde at 65°C for 6 hours. HDO of FL to the corresponding BPAOL over the Ir-ReOx/SiO2 catalyst was performed using 0.3 g of FL in 10 ml of cyclohexane solvent and 0.15 g of catalyst at 5 MPa H2 and 170°C for 12 hours.
Reagents | HAA reaction | HDO reaction | ||||
Entry | R1 | R2 | Products | Yield (%) | Products | Yield (%) |
1 | Methyl | n-Undecyl | C22-FL1 | 80 | C22-BPAOL1 | 91 |
2 | Ethyl | n-Undecyl | C24-FL1 | 82 | C24-BPAOL1 | 85 |
3 | n-Propyl | n-Undecyl | C26-FL1 | 94 | C26-BPAOL1 | 87 |
4 | n-Butyl | n-Undecyl | C28-FL1 | 89 | C28-BPAOL1 | 84 |
5 | n-Pentyl | n-Undecyl | C30-FL1 | 90 | C30-BPAOL1 | 87 |
6 | n-Hexyl | n-Undecyl | C32-FL1 | 89 | C32-BPAOL1 | 82 |
7* | n-Heptyl | n-Undecyl | C34-FL1 | 85 | C34-BPAOL1 | 83 |
8 | n-Pentyl | Methyl | C20-FL1 | 89 | C20-BPAOL1 | 87 |
9 | n-Pentyl | n-Pentyl | C24-FL2 | 93 | C24-BPAOL2 | 89 |
10 | n-Pentyl | n-Heptyl | C26-FL2 | 91 | C26-BPAOL2 | 91 |
11 | n-Pentyl | n-Nonyl | C28-FL2 | 87 | C28-BPAOL2 | 87 |
12† | n-Pentyl | 2-Ethylpentyl | C26-FL3 | 85 | C26-BPAOL3 | 87 |
13† | n-Hexyl | 2-Ethylpentyl | C28-FL3 | 86 | C28-BPAOL3 | 82 |
14† | n-Heptyl | 2-Ethylpentyl | C30-FL2 | 88 | C30-BPAOL2 | 81 |
*Eight hours.
†Twelve hours.